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Synthesis of cylclic porphyrin oligomers

Research Project

Project/Area Number 19K05626
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 35030:Organic functional materials-related
Research InstitutionIwate University

Principal Investigator

Kuzuhara Daiki  岩手大学, 理工学部, 准教授 (00583717)

Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2021: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2020: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2019: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsポルフィリン / 湾曲構造 / 金属錯体 / 環状化合物 / 包摂錯体 / 環状構造 / ホスト-ゲスト相互作用 / 超分子 / ホストーゲスト相互作用
Outline of Research at the Start

ダブルV字型構造を持つポルフィリン(2.1.2.1)を用いた環状ポルフィリン(2.1.2.1)多量体の合成法の確立と環状構造を活用した超分子構造の合成を目指す。具体的にはダブルV字型構造を持つポルフィリン(2.1.2.1)の構造的特徴を活用して、環サイズや架橋構造を制御した環状化合物や配位結合を用いた3Dカプセル型自己集合体の合成を試みる。

Outline of Final Research Achievements

Molecules with bowl shaped π-surfaces have been interested in a wide range of research fields, including organic electronics and biochemistry, because they exhibit different electronic properties on the inside and outside of the π-surface. In this study, we have developed a method for the synthesis of cyclic porphyrin (2.1.2.1) oligomers with various crosslinked structures. We found that dipyrrolylmaleimide is a useful starting material for the synthesis of cyclic porphyrin (2.1.2.1) oligomer. In addition, we succeeded in synthesizing pyridyl substituted porphyrin (2.1.2.1), which can form self-assemblies with metal ions.

Academic Significance and Societal Importance of the Research Achievements

機能性材料の性質は分子構造と密接に関連していることが知られている。その中でもπ曲面を持つ化合物は、平面型の分子とは異なった物性を示すため注目されている。本研究で着目したポルフィリン(2.1.2.1)は、ポルフィリンの広いπ共役面とV字型構造を併せ持つ特異な構造であり、環状構造を構築するためのビルディングブロックとしてやホスト分子としても有用であることを明らかにした。これらの結果は、今後π曲面化合物をセンシング材料や有機エレクトロニクス分野に応用するために大きく貢献するものである。

Report

(4 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • Research Products

    (50 results)

All 2022 2021 2020 2019

All Journal Article (16 results) (of which Int'l Joint Research: 8 results,  Peer Reviewed: 16 results,  Open Access: 1 results) Presentation (34 results) (of which Invited: 1 results)

  • [Journal Article] Synthesis, Characterization, and Electrochemistry of Copper Dibenzoporphyrin(2.1.2.1) Complexes2022

    • Author(s)
      Liu Ningchao、Osterloh W. Ryan、Huang Hongliang、Tang Xinyue、Mei Peifeng、Kuzuhara Daiki、Fang Yuanyuan、Pan Jianming、Yamada Hiroko、Qiu Fengxian、Kadish Karl M.、Xue Songlin
    • Journal Title

      Inorganic Chemistry

      Volume: 61 Issue: 8 Pages: 3563-3572

    • DOI

      10.1021/acs.inorgchem.1c03596

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Elucidating the Impact of Molecular Weight on Morphology, Charge Transport, Photophysics and Performance of All-Polymer Solar Cells2021

    • Author(s)
      Duyen K. Tran, Amelie Robitaille, I. Jo Hai, Xiaomei Ding, Daiki Kuzuhara, Tomoyuki Koganezawa, Yu-Cheng Chiu, Mario Leclerc, Samson A. Jenekhe
    • Journal Title

      Journal of Materials Chemistry A

      Volume: 8 Issue: 40 Pages: 21070-21083

    • DOI

      10.1039/d0ta08195g

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Controlled Fabrication and Characterization of Coronene Diimide‐Based Insoluble Thin Films Produced by Photoinduced Cyclization2021

    • Author(s)
      Ogawa Tomoya、Kuzuhara Daiki
    • Journal Title

      ChemPlusChem

      Volume: 86 Issue: 6 Pages: 852-857

    • DOI

      10.1002/cplu.202100131

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Binuclear Rhodium(I) Complex of a Dimethylvinylene-Bridged Distorted Hexaphyrin(2.1.2.1.2.1)2021

    • Author(s)
      Xue Songlin、Liu Ningchao、Mei Peifeng、Kuzuhara Daiki、Aratani Naoki、Qiu Fengxian、Yamada Hiroko
    • Journal Title

      Inorganic Chemistry

      Volume: 60 Issue: 21 Pages: 16070-16073

    • DOI

      10.1021/acs.inorgchem.1c02609

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Porphyrin(2.1.2.1) as a novel binucleating ligand: synthesis and molecular structures of mono- and di-rhodium(<scp>i</scp>) complexes2021

    • Author(s)
      Xue Songlin、Liu Ningchao、Mei Peifeng、Kuzuhara Daiki、Zhou Mingbo、Pan Jianming、Yamada Hiroko、Qiu Fengxian
    • Journal Title

      Chemical Communications

      Volume: 57 Issue: 95 Pages: 12808-12811

    • DOI

      10.1039/d1cc05641g

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Cyclic butadiyne-linked porphyrin(2.1.2.1) oligomers2020

    • Author(s)
      Kuzuhara Daiki、Furukawa Wataru、Aratani Naoki、Yamada Hiroko
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 24 Issue: 01n03 Pages: 489-497

    • DOI

      10.1142/s1088424619501931

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Effects of a Fluorinated Donor Polymer on the Morphology, Photophysics, and Performance of All-Polymer Solar Cells Based on Naphthalene Diimide Arylene Copolymer Acceptors2020

    • Author(s)
      Duyen K. Tran, Nagesh B. Kolhe, Ye-jin Hwang, Daiki Kuzuhara, Tomoyuki Koganezawa, Samson A. Jenekhe*
    • Journal Title

      ACS Applied Materials & Interfaces

      Volume: 12 Issue: 14 Pages: 16490-16502

    • DOI

      10.1021/acsami.0c01382

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Direct Correlation of Nanoscale Morphology and Device Performance to Study Photocurrent Generation in Donor-Enriched Phases of Polymer Solar Cells2020

    • Author(s)
      S. B. Dkhil, P. Perkhun, C. Luo, D. Moller, R. Alkarsifi, E. Barulina, Y.Alejandra A. Quiroz, O. Margeat, S. T. Dubas, T. Koganezawa, D.Kuzuhara, N. Yoshimoto, C. Caddeo, A. Mattoni, B. Zimmermann, U. Wurfel, M. Pfannmoller, S. Bals, J.Ackermann, and C. Videlot-Ackermann
    • Journal Title

      ACS Appl. Mater. Interfaces

      Volume: 12 Issue: 25 Pages: 28404-28415

    • DOI

      10.1021/acsami.0c05884

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Comparative Study of Selenophene- and Thiophene-Containing n-Type Semiconducting Polymers for High Performance All-Polymer Solar Cells2020

    • Author(s)
      Xiaomei Ding, Duyen K. Tran, Daiki Kuzuhara, Tomoyuki Koganezawa, and Samson A. Jenekhe
    • Journal Title

      Applied Polymer Materials

      Volume: 3 Issue: 1 Pages: 49-59

    • DOI

      10.1021/acsapm.0c00772

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers2020

    • Author(s)
      Songlin Xue, Daiki Kuzuhara, Naoki Aratani, Hiroko Yamada
    • Journal Title

      International Journal of Molecular Sciences

      Volume: 21 Issue: 21 Pages: 8041-8041

    • DOI

      10.3390/ijms21218041

    • NAID

      120007181846

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Layer-by-Layer Growth Control of Metal Organic Framework Thin Films Assembled on Polymer Films2020

    • Author(s)
      Hiroaki Ohara, Shunsuke Yamamoto, Daiki Kuzuhara, Tomoyuki Koganezawa, Hidetoshi Oikawa, and Masaya Mitsuishi
    • Journal Title

      ACS Applied Materials & Interfaces

      Volume: 12 Issue: 45 Pages: 50784-50792

    • DOI

      10.1021/acsami.0c13016

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a Porphyrin(2.1.2.1) Nanobelt and its Ability to Bind Fullerene2019

    • Author(s)
      Songlin Xue, Daiki Kuzuhara,* Naoki Aratani, Hiroko Yamada*
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 7 Pages: 2069-2072

    • DOI

      10.1021/acs.orglett.9b00329

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] New Random Copolymer Acceptors Enable Additive-Free Processing of 10.1% Efficient All-Polymer Solar Cells with Near Unity Internal Quantum Efficiency2019

    • Author(s)
      Nagesh B. Kolhe, Duyen Ky Tran, Hyunjong Lee, Daiki Kuzuhara, Noriyuki Yoshimoto, Tomoyuki Koganezawa, Samson A. Jenekhe
    • Journal Title

      ACS Energy Lett.

      Volume: 4 Issue: 5 Pages: 162-1170

    • DOI

      10.1021/acsenergylett.9b00460

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Solid-State, Near-Infrared to Visible Photon Upconversion via Triplet?Triplet Annihilation of a Binary System Fabricated by Solution Casting2019

    • Author(s)
      Abulikemu Aizitiaili、Sakagami Yusuke、Heck Claire、Kamada Kenji、Sotome Hikaru、Miyasaka Hiroshi、Kuzuhara Daiki、Yamada Hiroko
    • Journal Title

      ACS Applied Materials & Interfaces

      Volume: 11 Issue: 23 Pages: 20812-20819

    • DOI

      10.1021/acsami.9b04148

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Control of Aromaticity and cis ‐/ trans ‐Isomeric Structure of Non‐Planar Hexaphyrin(2.1.2.1.2.1) and Metal Complexes2019

    • Author(s)
      Xue Songlin、Kuzuhara Daiki、Aratani Naoki、Yamada Hiroko
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 58 Issue: 36 Pages: 12524-12528

    • DOI

      10.1002/anie.201906946

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] 2,7,12,17-Tetra(2,5-thienylene)-substituted porphycenes2019

    • Author(s)
      Kuzuhara Daiki、Nakaoka Haruka、Matsuo Kyohei、Aratani Naoki、Yamada Hiroko
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 23 Issue: 07n08 Pages: 898-907

    • DOI

      10.1142/s1088424619500743

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Presentation] ピレン含有油脂材料の結晶多形変化に伴う発光特性変化の評価2022

    • Author(s)
      松川奈愛, 葛原大軌
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] フタルイミド架橋カリックスピロールの合成と物性2022

    • Author(s)
      金子 真夕、菊池 翔、葛原 大軌
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 固体発光特性を示すピレン含有トリアシルグリセロールの合成2021

    • Author(s)
      松川奈愛, 葛原大軌
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 電子求引性置換基を有するポルフィリン誘導体の合成2021

    • Author(s)
      菊池翔, 谷山功起, 葛原大軌
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Synthesis and Photophysical Property of Pyrene Substituted Triacylglycerols2021

    • Author(s)
      松川奈愛, 葛原大軌
    • Organizer
      化学系学協会東北大会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Synthesis and Property of Conjugated Polymers by [2+2] Click Reaction2021

    • Author(s)
      金子 真夕、葛原 大軌
    • Organizer
      化学系学協会東北大会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 近赤外三重項-三重項消滅光アップコンバージョン固体系におけるルブレン誘導体から増感剤への逆エネルギー移動消光の研究2021

    • Author(s)
      澤あか音、ニィーティ トリバティ、クレア クック、玉井尚登、葛原大軌、山田容子、鎌田賢司
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] 光縮環反応を用いた拡張ペリレンジイミド不溶性薄膜の作製と評価2021

    • Author(s)
      万城目大和、小川倫弥、葛原大軌
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] 蒸着重合用有機半導体の合成2021

    • Author(s)
      金子 真夕、葛原 大軌
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] ポルフィリン (2.1.2.1)環状多量体の合成と物性2021

    • Author(s)
      上田有沙、葛原大軌、吉本則之
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] ケクレン誘導体の合成と物性2021

    • Author(s)
      岩渕 潤樹、葛原 大軌
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] トリアシルグリセロールを主骨格とした機能性油脂材料の合成2021

    • Author(s)
      松川 奈愛、葛原 大軌、吉本 則之
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] シッフ塩基架橋共有結合性有機構造体(COF)薄膜の作製と評価2021

    • Author(s)
      古川 皓啓, 葛原 大軌, 吉本 則之
    • Organizer
      第68回応用物理学会春季学術講演会
    • Related Report
      2020 Research-status Report
  • [Presentation] 非対称アルキル鎖を有するオリゴチオフェンの結晶構造及び物性評価2021

    • Author(s)
      佐藤 慧,葛原 大軌, 吉本 則之
    • Organizer
      第68回応用物理学会春季学術講演会
    • Related Report
      2020 Research-status Report
  • [Presentation] 電子線ホログラフィーによる有機EL素子内部の電位分布の可視化2020

    • Author(s)
      佐々木祐聖、佐藤岳志、山本和生、葛原大軌、吉本則之
    • Organizer
      日本顕微鏡学会第76回学術講演会
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      2020 Research-status Report
  • [Presentation] QCM/2D-GIXD 同時測定によるペンタセン薄膜成長における核形成過程の解析2020

    • Author(s)
      松原 亮介, 尾崎 幸潤, 阿部 優輝, 菊池 護,葛原 大軌, 吉本 則之, 小金澤 智之, 久保野 敦史
    • Organizer
      第81回応用物理学会秋季学術講演会
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  • [Presentation] チョクラルスキー法によるトリパルミチンの単結晶育成2020

    • Author(s)
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      第49回結晶成長国内会議
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  • [Presentation] 光縮環反応を用いた不溶性薄膜の作製と評価2020

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      第67回応用物理学会春季学術講演会
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  • [Presentation] 有機半導体の薄膜形成素過程に対するアルキル側鎖の影響2020

    • Author(s)
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      第67回応用物理学会春季学術講演会
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    • Author(s)
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      日本化学会第100春季年会
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    • Organizer
      日本化学会第100春季年会
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  • [Presentation] 電子線ホログラフィーによる有機積層膜の評価2019

    • Author(s)
      佐々木祐聖,佐藤岳志, 山本和生, 葛原大軌, 吉本則之
    • Organizer
      第80回応用物理学会秋季学術講演会
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  • [Presentation] 二次元斜入射X線回折法によるC10-4T薄膜の構造解析2019

    • Author(s)
      照井大貴,菊池護, 葛原大軌,渡辺剛,小金澤智之,廣沢一郎,吉本則之
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  • [Presentation] 2D-GIXDによるC10-4T薄膜の配向変化のその場観察2019

    • Author(s)
      阿部優輝, 葛原大軌, 小金澤智之, 吉本則之
    • Organizer
      第80回応用物理学会秋季学術講演会
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  • [Presentation] Synthesis of Porphyrin(2.1.2.1) Nanobelt and Nanoring2019

    • Author(s)
      葛原大軌
    • Organizer
      化学系学協会東北大会
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    • Invited
  • [Presentation] Fabrication of Insoluble Thin Films by Sholl Reaction2019

    • Author(s)
      小川倫弥, 葛原大軌, 吉本則之
    • Organizer
      化学系学協会東北大会
    • Related Report
      2019 Research-status Report
  • [Presentation] Molecular Orientations of Quarterthiophenes with Symmetric and Asymmetric Alkyl chains2019

    • Author(s)
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    • Organizer
      化学系学協会東北大会
    • Related Report
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  • [Presentation] 分子内環化反応によるペンタフェン誘導体の合成2019

    • Author(s)
      千葉裕矢, 葛原大軌, 吉本則之
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      第30回基礎有機化学討論会
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      2019 Research-status Report
  • [Presentation] Near-infrared-to-visible photon upconversion via triplet-triplet annihilation of a solid-state system fabricated by rapid drying casting2019

    • Author(s)
      Aizitiaili Abulikemu, Yusuke Sakagami, Claire Heck, Kenji Kamada, Hikaru Sotome, Hiroshi Miyasaka, Daiki Kuzuhara, Hiroko Yamada
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      JSAP-OSA joint symposia
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  • [Presentation] 電子線ホログラフィーによる有機EL素子内部の電位分布の可視化2019

    • Author(s)
      佐々木祐聖,佐藤岳志, 山本和生, 葛原大軌, 吉本則之
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      第48回結晶成長国内会議
    • Related Report
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  • [Presentation] 二次元斜入射X線回折法によるC10-4T薄膜の構造解析2019

    • Author(s)
      照井大貴,菊池護,葛原大軌,渡辺剛,小金澤智之,廣沢一郎,吉本則之
    • Organizer
      第48回結晶成長国内会議
    • Related Report
      2019 Research-status Report
  • [Presentation] チョクラルスキー法によるベンゾフェノン単結晶育成2019

    • Author(s)
      伊藤大生,菊池護, 葛原大軌, 吉本則之
    • Organizer
      第48回結晶成長国内会議
    • Related Report
      2019 Research-status Report

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Published: 2019-04-18   Modified: 2023-01-30  

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